In August 2015, HBO commissioned two pilots from Simon's company Blown Deadline Productions. The first drama, The Deuce, about the New York porn industry in the 1970s and 1980s, stars Maggie Gyllenhaal and co-producer James Franco and began airing in September 2017. The second drama is an untitled program exploring a "detailed examination of partisanship" and money in Washington politics, to be co-produced with Carl Bernstein.[4]

Simon was born in Washington, D.C., the son of Dorothy Simon (née Ligeti), a homemaker, and Bernard Simon, a former journalist and then public relations director for B'nai B'rith for 20 years.[5][6][7][8] In March 1977, when Simon was still in high school, Simon's father was one of a group of over 140 people held hostage (and later released) in Washington, D.C. by former national secretary of the Nation of Islam Hamaas Abdul Khaalis in the Hanafi Siege.[9][10][11]

Simon was raised in a Jewish family with roots that originated in Eastern Europe and Hungary (his maternal grandfather had changed his surname from "Leibowitz" to "Ligeti").[7][12] He has a brother, Gary Simon, and a sister, Linda Evans, who died in 1990.[8]

Upon leaving college, Simon worked as a police reporter at The Baltimore Sun from 1982 to 1995.[16] He spent most of his career covering the crime beat.[16][17] A colleague has said that Simon loved journalism and felt it was "God's work".[17] Simon says that he was initially altruistic and was inspired to enter journalism by the Washington Post's coverage of Watergate but became increasingly pragmatic as he gained experience.[17] Later in his career he aimed to tell the best possible story without "cheating it".[17]

Simon was a union captain when the writing staff went on strike in 1987 over benefit cuts.[18] He remained angry after the strike ended and began to feel uncomfortable in the writing room.[18] He searched for a reason to justify a leave of absence and settled on the idea of writing a novel.[18] "I got out of journalism because some sons of bitches bought my newspaper and it stopped being fun," says Simon.[19]

In 1988, disillusioned, Simon took a year's leave to go into the Baltimore Police Department Homicide Unit to write a book.[20]

Simon's leave of absence from The Sun resulted in his first book Homicide: A Year on the Killing Streets (1991). The book was based on his experiences shadowing the Baltimore Police Department homicide unit during 1988.[16] The idea came from a conversation on Christmas Eve 1985 in the unit office, where Det. Bill Lansey told him, "If someone just wrote down what happens in this place for one year, they'd have a goddamn book."[18] Simon approached the police department and the editors of the paper to receive approval. The detectives were initially slow to accept him, but he persevered in an attempt to "seem … like part of the furniture". However, he soon ingratiated himself with the detectives, saying in the closing notes of the book, "I shared with the detectives a year's worth of fast-food runs, bar arguments and station house humor: Even for a trained observer, it was hard to remain aloof."[17] During one instance, Simon even assisted with an arrest. Two detectives Simon was riding with pulled their car to a curb to apprehend two suspects, but Detective Dave Brown got his trenchcoat caught in a seat belt when he tried to exit the car. Brown told Simon to assist Detective Terry McLarney himself, and Simon helped apprehend and search one of the suspects.[21]

The book won the 1992 Edgar Award for Best Fact Crime book.[22] The Associated Press called it "a true-crime classic".[21] The Library Journal also highly recommended it, and Newsday described it as "one of the most engrossing police procedural mystery books ever written".[21] Simon credits his time researching the book as altering his writing style and informing later work. He learned to be more patient in research and writing, and said a key lesson was not promoting himself but concentrating on his subjects.[17] Simon told Baltimore's City Paper in 2003 that Homicide was not traditional journalism. "I felt Homicide the book and The Corner were not traditional journalism in the sense of coming from some artificially omniscient, objective point of view," said Simon. "They're immersed in the respective cultures that they cover in a way that traditional journalism often isn't."[19]

The publishers of Homicide: A Year on the Killing Streets were eager for a screen adaptation and submitted it to numerous directors but there was little interest.[18] Simon suggested that they send the book to Baltimore native and film director Barry Levinson. Levinson's assistant Gail Mutrux enjoyed the book and both she and Levinson became attached as producers.[18] The project became the award-winning TV series Homicide: Life on the Street (1993–1999), on which Simon worked as a writer and producer.[16]

Simon was asked by Mutrux to write the show's pilot episode but declined, feeling he did not have the necessary expertise.[23] He collaborated with his old college friend David Mills to write the season two premiere "Bop Gun".[17][24] The episode was based on a story by executive producer Tom Fontana and featured Robin Williams in a guest starring role that garnered the actor an Emmy nomination. Simon and Mills won the WGA Award for Best Writing in a Drama for the episode.[17] Simon also received Austin Film Festival's Outstanding Television Writer Award in 2010.

Simon left his job with the Baltimore Sun in 1995 to work full-time on Homicide: Life on the Street during the production of the show's fourth season. Simon wrote the teleplay for the season four episodes "Justice: Part 2"[25] and "Scene of the Crime" (with Anya Epstein).[26] For season five he was the show's story editor and continued to contribute teleplays writing the episodes "Bad Medicine"[27] and "Wu's on First?" (again with Epstein).[28] He was credited as a producer on the show's sixth and seventh seasons. He wrote the teleplays for parts two and three of the sixth season premiere "Blood Ties"[29][30] (the latter marking his third collaboration with Epstein) and provided the story for the later sixth season episodes "Full Court Press"[31] and "Finnegan's Wake" (with James Yoshimura).[32] He provided the story for the seventh season episodes "Shades of Gray" (with Julie Martin),[33] "The Same Coin" (again with Yoshimura)[34] and "Self Defense" (with Eric Overmyer).[35] Simon wrote the story and teleplay for the seventh season episodes "The Twenty Percent Solution"[36] and "Sideshow: Part 2".[37] Simon, Martin and teleplay writer T. J. English won the Humanitas Prize in the 60 minutes category for the episode "Shades of Gray".[38] Simon was nominated for a second WGA Award for Best Writing in a Drama for his work on "Finnegan's Wake" with Yoshimura and Mills (who wrote the teleplay).[39]

Simon has said that he thought the show was a "remarkable drama" but that it did not reflect the book.[18] He has also said that when writing for the show he had to put his experiences of the real detectives aside as the characters became quite different, particularly in their more philosophical approach to the job.[23] Simon said that TV must find shorthand ways of referencing anything real.[17]

In 1997 he co-authored, with Ed Burns, The Corner: A Year in the Life of an Inner-City Neighborhood, the true account of a West Baltimore community dominated by a heavy drug market.[40][41] Simon credits his editor John Sterling with the suggestion that he observe a single drug corner.[16] He took a second leave of absence from the Baltimore Sun in 1993 to research the project.[17][42] Simon became close to one of his subjects, drug addict Gary McCullough, and was devastated by his death while he was writing the project.[17] Simon says that he approached the research with the abstract idea that his subjects may die because of their addictions but it was not possible to fully prepare for the reality.[17] He remains grateful to his subjects saying "This involved people's whole lives, there's no privacy in it. That was an enormous gift which many, many people gave us. Even the most functional were at war with themselves. But they were not foolish people. And they made that choice."[17]

The Corner was named a Notable Book of the Year by The New York Times.[43] Simon again returned to his journalism career after finishing the book but felt further changed by his experiences. He said he "was less enamored of the braggadocio, all that big, we're-really-having-an-impact talk" and no longer believed that they were making a difference; he left his job at The Sun within a year for work on NBC's Homicide.[17]

Again he worked with Ed Burns on creating the show. Originally they set out to create a police drama loosely based on Burns' experiences when working on protracted investigations of violent drug dealers using surveillance technology.[46] During this time Burns had often faced frustration with the bureaucracy of the police department, which Simon equated with his own ordeals as a police reporter for The Baltimore Sun.[47] Writing against the background of current events, including institutionalized corporate crime at Enron and institutional dysfunction in the Catholic Church, the show became "more of a treatise about institutions and individuals than a straight cop show."[48]

They chose to take The Wire to HBO because of their existing working relationship from The Corner. Owing to its reputation for exploring new areas, HBO was initially dubious about including a cop drama in their lineup, but eventually agreed to produce the pilot[48][49] after ordering a further two scripts to see how the series would progress.[50]Carolyn Strauss, the president of HBO entertainment, has said that Simon's argument that the most subversive thing HBO could do was invade the networks' "backyard" of police procedurals helped to persuade them.[16]

The theme of institutional dysfunction was expanded across different areas of the city as the show progressed. The second season focused on the death of working-class America through examination of the city ports.[51] The third season "reflects on the nature of reform and reformers, and whether there is any possibility that political processes, long calcified, can mitigate against the forces currently arrayed against individuals." [51] For the fourth season Simon again turned to Burns' experience, this time his second career as a Baltimore public school teacher in examining the theme of education.[16][52] The fifth season looked at the media, as well as continuing themes such as politics from earlier seasons.

Simon was reunited with his The Corner producers Robert F. Colesberry and Nina K. Noble on The Wire.[45] Simon credits Colesberry for achieving the show's realistic visual feel because of his experience as a director.[53] They recruited Homicide star and director Clark Johnson to helm the pilot episode.[53] The completed pilot was given to HBO in November 2001.[50] Johnson returned to direct the second episode when the show was picked up,[53] and would direct the series finale as well, in addition to starring in the fifth season.

Simon approached acclaimed crime fiction authors to write for The Wire. He was recommended the work of George Pelecanos by a colleague while working at the Baltimore Sun because of similarities between their writing. The two writers have much in common including a childhood in Silver Spring, attendance at the University of Maryland and their interest in the "fate of the American city and the black urban poor."[50] Simon did not read Pelecanos initially because of territorial prejudice; Pelecanos is from Washington.[18] Once Simon received further recommendations including one from his wife Laura Lippman he tried Pelecanos' novel The Sweet Forever and changed his mind.[50] He sought out Pelecanos when recruiting writers for The Wire. The two met at the funeral of a mutual friend shortly after Simon delivered the pilot episode.[50] Simon pitched Pelecanos the idea of The Wire as a novel for television about the American city as Pelecanos drove him home.[50] Pelecanos became a regular writer[54] and later a producer for the show's second[55] and third seasons.[56] Simon and Pelecanos collaborated to write the episode "Middle Ground"[57][58] which received the show's first Emmy nomination, in the category Outstanding Writing for a Drama Series.[59]

Pelecanos left the production staff following the third season to focus on his next novel; Simon has commented that he missed having him working on the show full-time but was pleased that he continued to write for them and was a fan of the resultant book The Night Gardener.[60] Similar to Simon's own experience in researching Homicide Pelecanos spent time embedded with the Washington DC homicide unit to research the book.

Crime novelist Dennis Lehane has also written for the series starting with the third season.[56][61] Lehane has commented that he was impressed by Simon and Burns' ear for authentic street slang.[50]

Eric Overmyer was brought in to fill the role of Pelecanos as a full-time writer producer.[60][62] He had previously worked with Simon on Homicide where the two became friends.[60] Simon has said that he was impressed with Overmyer's writing particularly in synthesizing the story for "Margin of Error" as the episode is the height of the show's political storyline but must also progress other plot threads.[60]

Simon and his writing staff were nominated for the Writers Guild of America Award for Best Dramatic Series at the February 2009 ceremony for their work on the fifth season.[63] Simon and Burns collaborated to write the series finale "-30-" which received the show's second Emmy nomination, again in the category Outstanding Writing for a Drama Series.[64]

Simon has stated that he finds working with HBO more comfortable than his experiences with NBC on Homicide and that HBO is able to allow greater creative control because it is dependent on subscribers rather than on viewing figures.[40] He has said that he feels unable to return to network television because he felt pressure to compromise storytelling for audience satisfaction.[18]

Simon collaborated with Eric Overmyer again on Treme,[66] a project about musicians in post-Katrina New Orleans.[50] Overmyer lives part-time in New Orleans, and Simon believed his experience would be valuable in navigating the "ornate oral tradition" of the city's stories.[50] Simon also consulted with New Orleans natives Donald Harrison Jr., Kermit Ruffins, and Davis Rogan while developing the series.[67] The show focuses on a working-class neighborhood, and is smaller in scope than The Wire. The series premiered on April 11, 2010 on HBO and ran for four seasons.

Treme is named after the Faubourg Treme neighborhood in New Orleans that is home to many of the city's musicians.[66] Simon has stated that the series will explore beyond the music scene to encompass political corruption, the public housing controversy, the criminal-justice system, clashes between police and Mardi Gras Indians, and the struggle to regain the tourism industry after the storm.[68] One of the principal characters in the pilot script runs a restaurant.[67] The series was filmed on location and was expected to provide a boost to the New Orleans economy.[68] Simon's casting of the show mirrored that of The Wire in using local actors wherever possible.[67]Wendell Pierce, who had previously played Bunk Moreland on The Wire, stars in the series. Clarke Peters, also of The Wire, is another series regular. Many other stars of The Wire have appeared in Treme, these include Steve Earle, Jim True-Frost, James Ransone, and Anwan Glover.[69]

In 2014, HBO greenlit production for Simon's next project Show Me a Hero, a six-hour miniseries co-written with William F. Zorzi and the episodes directed by Academy Award-winner Paul Haggis. The miniseries is an adaptation of the nonfiction book of the same name by Lisa Belkin and tells the story of Nick Wasicsko, the youngest big-city mayor in the nation who finds himself thrust into racial controversy when a federal court orders to build a small number of low-income housing units in the white neighborhoods of Yonkers, New York.[70]Oscar Isaac stars as Wasicsko and leads a cast, which includes Catherine Keener, Jim Belushi, Bob Balaban and Winona Ryder. The miniseries premiered on August 16, 2015.[71]

The Deuce is a 2017 drama television series set in Times Square, New York focusing on the rise of the porn industry in the 1970s-80s. Created and written by Simon along with frequent collaborator George Pelecanos, the series pilot began shooting in October 2015.[72] It was picked up to series in January 2016. It premiered on September 10, 2017 and is broadcast by the premium cable network HBO in the United States.[73]

The Deuce tells the story of the legalization and ensuing rise of the porn industry in New York beginning in the 1970s and its ongoing rise through the mid-1980s. Themes explored include the rise of HIV, the violence of the drug epidemic and the resulting real estate booms and busts that coincided with the change.

The Good Friday Plot: Miniseries about Abraham Lincoln[80] based upon Manhunt: The Twelve-Day Chase for Lincoln's Killer by James L. Swanson[81] and American Brutus: John Wilkes Booth and the Lincoln Conspiracies by Michael W. Kauffman[82]

Capitol Hill: A collaboration with Carl Bernstein set in Capitol Hill, it examines partisanship and the role money plays in influencing national governance.[72]

Simon is known for his realistic dialogue and journalistic approach to writing.[50] He says that authenticity is paramount and that he writes not with a general audience in mind but with the opinions of his subjects as his priority.[50] He has described his extensive use of real anecdotes and characters in his writing as "stealing life".[87]

In a talk that Simon gave to a live audience in April 2007 at the Creative Alliance's storytelling series, Simon disclosed that he had started writing for revenge against John Carroll and Bill Marimow, the two most senior editors at The Baltimore Sun when Simon was a reporter at the paper.[88] Simon said he had watched Carroll and Marimow "single-handedly destroy" the newspaper and that he spent over ten years trying to get back at them.[88]

Anything I've ever accomplished as a writer, as somebody doing TV, anything I've ever done in life, down to, like, cleaning up my room, has been accomplished because I was going to show people that they were fucked up, wrong, and that I was the fucking center of the universe and the sooner they got hip to that, the happier they would all be.[88]

One of the actions Simon took was to name a character in The Wire after Marimow and make the character "a repellent police-department toady."[89] Carroll left the Baltimore Sun to become editor at the Los Angeles Times and resigned in 2005 after budget cuts were announced.[88] "He stands up like a [bleeping] hero, takes a bullet," said Simon.[88] In 2006 Marimow was diagnosed with prostate cancer, something that Simon said "took the edge off" his grudge.[88] Carroll and Marimow "were fuel for 10 years of my life. ... And now, I got nothing," Simon said.[88]

When asked about these comments, Simon said that he had spoken with "some hyperbole and, I hope, comic effect", adding that his basic viewpoint was: "that simple revenge is both empty and beside the point and that a good story carefully told has to speak to larger themes. You do not tell an ornate, careful story over ten hours of HBO airtime merely to bust on any given soul."[88]

In an interview in Reason in 2004, Simon said that since leaving the newspaper business he has become more cynical about the power of journalism.[40] "One of the sad things about contemporary journalism is that it actually matters very little. The world now is almost inured to the power of journalism. The best journalism would manage to outrage people. And people are less and less inclined to outrage," said Simon.[40] "I've become increasingly cynical about the ability of daily journalism to effect any kind of meaningful change. I was pretty dubious about it when I was a journalist, but now I think it's remarkably ineffectual."[40]

While testifying at a 2009 Senate hearing regarding the future of journalism in America, Simon indicted what he saw as poor online journalism, calling the phrase citizen journalist "Orwellian to [his] ears."[90] Simon ended his testimony by declaring, "I don't think anything can be done to save high-end journalism."[90]

Simon has described himself as a social democrat, broadly supporting the existence of capitalism whilst opposing "raw, unencumbered capitalism, absent any social framework, absent any sense of community, without regard to the weakest and most vulnerable classes in society", which he described as "a recipe for needless pain, needless human waste, (and) needless tragedy". He has criticised the idea of trickle-down economics.[91]

In 2013, Simon compared the global surveillance disclosures uncovered by Edward Snowden to a 1980s effort by the City of Baltimore to record the numbers dialed from all pay phones.[92] The city believed that drug traffickers were using pay phones and pagers, and a municipal judge allowed the city to record the dialed numbers. The placement of the payphone number recorders formed the basis of The Wire's first season. Simon argued that the media attention regarding the surveillance disclosures is a "faux scandal."[92][93]

During a November 2013 speech at the Festival of Dangerous Ideas in Sydney, he said that America has become "a horror show" of savage inequality as a result of capitalism run amok, and that "unless we reverse course, the average human being is worth less on planet Earth. Unless we take stock of the fact that maybe socialism and the socialist impulse has to be addressed again; it has to be married as it was married in the 1930s, the 1940s and even into the 1950s, to the engine that is capitalism."[94][95]

Simon has also spoken out publicly against crime journalist Kevin Deutsch, disputing the portrayal of Baltimore's illegal drug trade in Deutsch's book, Pill City: How Two Honor Roll Students Foiled the Feds and Built a Drug Empire. Simon has described the book as a "a wholesale fabrication."[96]

^Margaret Talbot (2007). "Stealing Life". The New Yorker. Retrieved 14 October 2007. Simon's gift is in recognizing an anecdote [...] for the found parable that it is — "stealing life," as he once described it to me — and knowing which parts to steal.